EP0697211B1 - Utilisation d'un sel métallique dans un procédé de teinture en deux temps mettant en oeuvre un composé indolique - Google Patents

Utilisation d'un sel métallique dans un procédé de teinture en deux temps mettant en oeuvre un composé indolique Download PDF

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Publication number
EP0697211B1
EP0697211B1 EP19950401567 EP95401567A EP0697211B1 EP 0697211 B1 EP0697211 B1 EP 0697211B1 EP 19950401567 EP19950401567 EP 19950401567 EP 95401567 A EP95401567 A EP 95401567A EP 0697211 B1 EP0697211 B1 EP 0697211B1
Authority
EP
European Patent Office
Prior art keywords
use according
composition
manganese
metallic salt
zinc
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Revoked
Application number
EP19950401567
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German (de)
English (en)
French (fr)
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EP0697211A1 (fr
Inventor
Henri Samain
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LOreal SA
Original Assignee
LOreal SA
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Application filed by LOreal SA filed Critical LOreal SA
Publication of EP0697211A1 publication Critical patent/EP0697211A1/fr
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4913Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
    • A61K8/492Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/10Preparations for permanently dyeing the hair

Definitions

  • the subject of the present invention is the use of a metal salt in a process for dyeing keratin fibers in two stages using an indole compound.
  • 5,6-Dihydroxyindole is generally used in aqueous compositions with which it is possible to dye keratin fibers and in particular the hair, this dyeing being able to be carried out in several times or gradually without any other oxidizing agent than oxygen. the air. It is possible in this way to repigment the hair starting from relatively light shades by an application of the product, even in more and more sustained shades, by superposition of the applications.
  • a subject of the invention is therefore the use of a metal salt, in a two-stage dyeing process for keratin fibers and in particular human keratin fibers such as the hair, firstly using a composition ( A) containing, in a medium suitable for dyeing, at least one indolic compound of formula (I) below: in which : R 1 , R 2 , R 3 , R 4 ; identical or different, denote a hydrogen atom or a C 1 -C 4 alkyl radical, R 1 , R 2 , R 3 denoting hydrogen when R 4 denotes a C 1 -C 4 alkyl radical, and in a second step , a composition (B) containing in a medium suitable for dyeing at least one metal salt chosen from compounds having a catalytic activity of oxidation by air and whose normal oxidation-reduction potential E 0 is less than - 0.25V, in order to obtain colorations in gray shades which do not change over time.
  • a composition ( A) containing
  • the Applicant has observed in particular that the colorings obtained are particularly resistant to light and this is superior to the state of the art, that is to say that the light does not cause significant degradation over time of the colorations. obtained. These colors also have good resistance to repeated washing and perspiration.
  • the alkyl radical preferably denotes methyl or ethyl and R 1 , R 2 and R 3 do not simultaneously denote a C 1 -C 4 alkyl radical.
  • the preferred indole compounds of formula (I) are chosen from 5,6-dihydroxyindole, 2-methyl 5,6-dihydroxyindole, 3-methyl 5,6-dihydroxyindole, 1-methyl 5,6-dihydroxyindole, 2,3-dimethyl 5,6-dihydroxyindole, 5-methoxy 6-hydroxyindole.
  • a particularly preferred indole compound of formula (I) is 5,6-dihydroxyindole.
  • the particular metal salt (s) of the invention can be used in dissolved or dispersed form and are more particularly chosen from manganese, zinc, iron and / or cobalt salts. These salts can be used alone or as a mixture.
  • Examples of such compounds are manganese diacetate tetrahydrate, manganese dichloride and its hydrates, manganese dihydrogen carbonate, manganese acetylacetonate, manganese triacetate and its hydrates, manganese trichloride, zinc dichloride, zinc diacetate dihydrate, zinc carbonate, zinc dinitrate, zinc sulfate, iron dichloride, iron sulfate, iron diacetate, cobalt diacetate tetrahydrate, cobalt carbonate, cobalt dichloride , cobalt dinitrate, cobalt sulfate heptahydrate.
  • Manganese diacetate tetrahydrate and zinc dichloride are particularly preferred.
  • the metal salt or salts used according to the invention are generally used in proportions of between 0.001 and 4% by weight of metal equivalent relative to the total weight of the composition (B) and preferably between 0.005 and 2% by weight of metal equivalent relative to the total weight of the composition (B).
  • compositions (A) and (B) are preferably separated by a rinsing step.
  • Composition (A) containing at least one indolic compound of formula (I) is applied to keratin fibers and in particular human keratin fibers such as the hair with an exposure time generally between 15 seconds and 30 minutes.
  • Composition (B) containing the metal salt or salts of the invention is applied to keratin fibers and in particular human keratin fibers such as the hair with an exposure time generally between 15 seconds and 30 minutes.
  • the dyeing process using at least one metal salt of the invention is carried out using no other oxidant than oxygen in the air.
  • the indole compound (s) of formula (I) used according to the invention are generally used in proportions sufficient to repigment the keratin fibers and in particular the hair. These proportions are preferably between 0.1 and 5% by weight and even more preferably between 0.2 and 3% by weight relative to the total weight of the composition (A).
  • compositions (A) and (B) are preferably aqueous or consist of a mixture of water and a cosmetically acceptable solvent.
  • compositions contain a cosmetically acceptable solvent
  • this can be chosen from lower C 1 -C 4 alcohols such as ethanol, propyl alcohol, isopropyl alcohol, tert-butyl alcohol; glycols such as ethylene glycol, propylene glycol; glycol ethers such as monomethyl, monoethyl or monobutyl ethers of ethylene glycol, monomethyl ethers of propylene glycol and dipropylene glycol; lower esters such as methyl lactate and ethylene glycol monoethyl ether acetate.
  • the particularly preferred solvents are chosen from ethanol and propylene glycol.
  • the solvents preferably represent from 0.5 to 50% by weight and preferably from 2 to 20% by weight relative to the total weight of the composition (A) or (B).
  • composition (A) used according to the invention generally has a pH of between 5 and 10 and preferably between 7 and 9.5. This pH is adjusted using basifying or acidifying agents conventionally used in the field of hair dyeing.
  • basifying agents there may be mentioned by way of example, ammonia, alkanolamines such as for example mono-, di- and triethanolamines and their derivatives, sodium or potassium hydroxides such as for example sodium hydroxide and potash, alkylamines, alkali or ammonium carbonates.
  • alkanolamines such as for example mono-, di- and triethanolamines and their derivatives
  • sodium or potassium hydroxides such as for example sodium hydroxide and potash
  • alkylamines alkali or ammonium carbonates.
  • acidifying agents mention may be made, for example, of orthophosphoric acid, lactic acid, acetic acid, tartaric acid, hydrochloric acid and citric acid.
  • composition (B) used according to the invention generally has a pH of between 5 and 11 and preferably between 7 and 10. This pH is adjusted using basifying or acidifying agents conventionally used in the field of dyeing of hair and as described above.
  • compositions (A) and / or (B) used according to the invention can be in the form of more or less thickened lotions, gels, shampoos, emulsions such as milks and creams or they can be propelled in the form of aerosol foams.
  • the composition (A) is in the form of a gel and the composition (B) in the form of a shampoo.
  • composition (A) in the form of a gel and containing the indole compound (s) of formula (I) is applied to the keratin fibers with an exposure time varying between 15 seconds and 30 minutes then after rinsing at water, composition (B) in the form of a shampoo and containing the metal salt or salts used according to the invention is emulsified on the fibers for a few seconds to a few minutes. The fibers are then rinsed and dried.
  • compositions (A) and / or (B) may also contain at least one adjuvant chosen from the adjuvants conventionally used in the compositions for the hair dyeing such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or their mixtures, mineral or organic thickening agents, antioxidants, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents, film-forming agents, preserving agents, opacifying agents, sun filters, etc.
  • adjuvants chosen from the adjuvants conventionally used in the compositions for the hair dyeing such as anionic, cationic, nonionic, amphoteric, zwitterionic surfactants or their mixtures, mineral or organic thickening agents, antioxidants, penetration agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents, film-forming agents, preserving agents, opacifying agents, sun filters, etc.
  • composition A is prepared: - 5,6-dihydroxyindole 0.5 g - Xanthan gum 1.8g - Alkylpolyglucoside in aqueous solution at 60% of active material (MA) sold by the company SEPPIC 4 g - Tartaric acid 0.35 g - Ethanol 12 g - Triethanolamine qs pH 8.5 - Demineralized water qs 100g
  • composition (B 1 ) is prepared, which is a shampoo not forming part of the invention: - Copra acid monoisopropanolamide sold by the company ALLBRIGHT ET WILSON SAINT MIHIEL 2.5g - Monoethanolamine lauryl ether sulfate in an aqueous solution containing 28% of MA 40 g - Cocoylbetaine in 32% aqueous solution of MA sold by the company HENKEL 10 g - Ricinoleic monoethanolamide monosulfosuccinate, disodium salt sold by the company WITCO 2 g - Sodium hydroxide qs pH 9.5 - Perfume qs - Demineralized water qs 100g
  • composition (B 2 ) is prepared, which is a shampoo forming part of the invention: - Copra acid monoisopropanolamide sold by the company ALLBRIGHT ET WILSON SAINT MIHIEL 2.5g - Monoethanolamine lauryl ether sulfate in an aqueous solution containing 28% of MA 40 g - Manganese diacetate, tetrahydrate 1 g - Cocoylbetaine in 32% aqueous solution of MA sold by the company HENKEL 10 g - Ricinoleic monoethanolamide monosulfosuccinate, disodium salt sold by the company WITCO 2 g - Sodium hydroxide qs pH 9.5 - Perfume qs - Demineralized water qs 100g
  • Composition (A) is applied to two strands of natural gray hair containing 90% white hair for 10 minutes and then rinsed with water.
  • the composition (B 1 ) is then applied to the first lock, which is emulsified for approximately 30 seconds and then rinsed with water.
  • the composition (B 2 ) is then applied to the second lock, which is emulsified for approximately 30 seconds and then rinsed with water. The two locks are then dried.
  • the two locks have an identical metallic gray coloration.
  • the two locks are then left in the open air and in natural light for a period of three weeks. It is then observed that the lock having undergone shampooing with the composition (B 1 ) not forming part of the invention has a coloration which has become golden gray while the lock having undergone the shampoo with the composition (B 2 ) forming of the invention always has a metallic gray coloring.
  • composition (B 3 ) is prepared, which is a shampoo forming part of the invention: - Copra acid monoisopropanolamide sold by the company ALLBRIGHT ET WILSON SAINT MIHIEL 2.5g - Monoethanolamine lauryl ether sulfate in an aqueous solution containing 28% of MA 40 g - Zinc dichloride 1 g - Cocoylbetaine in 32% aqueous solution of MA sold by the company HENKEL 10 g - Ricinoleic monoethanolamide monosulfosuccinate, disodium salt sold by the company WITCO 2 g - Sodium hydroxide qs pH 9.5 - Perfume qs - Demineralized water qs 100g
  • composition (A) as described in Example 1 above is applied to two locks of natural gray hair containing 90% white for 10 minutes and then rinsed with water.
  • the composition (B 1 ) as described above in Example 1 is then applied to the first lock, which is emulsified for approximately 30 seconds and then rinsed with water.
  • the composition (B 3 ) is then applied which is emulsified for approximately 30 seconds and then rinsed with water. The two locks are then dried.
  • the two locks are then again subjected to the treatment described above and then they are left in the open air and in natural light for a period of three weeks.
  • L indicates clarity. The higher the value of L, the lighter the color. Conversely, the lower the value of L, the darker the color and therefore more powerful.
  • Hue and saturation are expressed by a and b.
  • a and b indicate two color axes, a red green axis and b yellow blue axis.
  • a positive value of a corresponds to a red tint the more saturated the higher the absolute value of a.
  • a negative value of a corresponds to a green tint the more saturated the higher the absolute value of a.
  • a positive value of b corresponds to a yellow tint the more saturated the higher the absolute value of b.
  • a negative value of b corresponds to a blue tint the more saturated the higher the absolute value of b.
  • the locks dyed with the composition B 3 forming part of the invention After three weeks, the locks dyed with the composition B 3 forming part of the invention have a color that has changed less than that of the locks dyed with the composition B 1 not forming part of the invention.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Coloring (AREA)
EP19950401567 1994-07-22 1995-06-29 Utilisation d'un sel métallique dans un procédé de teinture en deux temps mettant en oeuvre un composé indolique Revoked EP0697211B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9409116A FR2722684A1 (fr) 1994-07-22 1994-07-22 Utilisation d'un sel metallique dans un procede de teinture en deux temps mettant en oeuvre un compose indolique
FR9409116 1994-07-22

Publications (2)

Publication Number Publication Date
EP0697211A1 EP0697211A1 (fr) 1996-02-21
EP0697211B1 true EP0697211B1 (fr) 1996-10-09

Family

ID=9465675

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19950401567 Revoked EP0697211B1 (fr) 1994-07-22 1995-06-29 Utilisation d'un sel métallique dans un procédé de teinture en deux temps mettant en oeuvre un composé indolique

Country Status (4)

Country Link
EP (1) EP0697211B1 (enrdf_load_stackoverflow)
DE (1) DE69500063T2 (enrdf_load_stackoverflow)
ES (1) ES2095788T3 (enrdf_load_stackoverflow)
FR (1) FR2722684A1 (enrdf_load_stackoverflow)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL195678B1 (pl) 1998-03-06 2007-10-31 Oreal Sposób farbowania włókien keratynowych, kompozycja do farbowania utleniającego, kompozycja utleniająca oraz wieloprzedziałowy zestaw do farbowania
FR2779055B1 (fr) * 1998-05-28 2001-05-04 Oreal Composition de teinture directe pour fibres keratiniques avec un colorant direct cationique et un polyol et/ou un ether de polyol
FR2780882B1 (fr) * 1998-07-09 2001-04-06 Oreal Composition de teinture pour fibres keratiniques avec un colorant direct cationique et un polymere epaississant
DE102015212324A1 (de) * 2015-07-01 2017-01-05 Henkel Ag & Co. Kgaa "Leistungsstarke Farbschutz-Haarbehandlungsmittel mit einem Aminosäuresalz "

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL254075A (enrdf_load_stackoverflow) * 1959-07-24
LU86346A1 (fr) * 1986-03-06 1987-11-11 Oreal Compositions tinctoriales pour fibres keratiniques a base de derives d'indole et composes nouveaux
CA1324320C (en) * 1988-03-31 1993-11-16 Thomas M. Schultz Use of n-substituted-5,6-dihydroxyindoles as a hair coloring agent
CA1333690C (en) * 1988-05-12 1994-12-27 Thomas Matthew Schultz Process for dyeing hair by the sequential treatment with metal ion containing composition and dye composition containing 5,6-dihydroxyindole-2-carboxylic acid
DE4208297A1 (de) * 1992-03-16 1993-09-23 Henkel Kgaa Faerben von keratinischen fasern mit indolinen unter metallkatalyse
FR2700266B1 (fr) 1993-01-11 1995-03-03 Oreal Utilisation de sel de magnésium dans un procédé de teinture des fibres kératiniques mettant en Óoeuvre le 5,6-dihydroxyindole ou l'un de ses dérivés, procédés et compositions les mettant en Óoeuvre.
US5368610A (en) * 1993-04-20 1994-11-29 Clairol Incorporated Use of metal salts and chelates together with chlorites as oxidants in hair coloring

Also Published As

Publication number Publication date
EP0697211A1 (fr) 1996-02-21
FR2722684A1 (fr) 1996-01-26
DE69500063D1 (de) 1996-11-14
DE69500063T2 (de) 1997-02-13
FR2722684B1 (enrdf_load_stackoverflow) 1997-03-07
ES2095788T3 (es) 1997-02-16

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